CATALYTIC ASYMMETRIC ALLYLATION USING A CHIRAL (ACYLOXY)BORANE COMPLEX AS A VERSATILE LEWIS-ACID CATALYST

被引：167

作者：

ISHIHARA, K ^{[1
]}

MOURI, M ^{[1
]}

GAO, QZ ^{[1
]}

MARUYAMA, T ^{[1
]}

FURUTA, K ^{[1
]}

YAMAMOTO, H ^{[1
]}

机构：

[1] NAGOYA UNIV,SCH ENGN,CHIKUSA KU,NAGOYA 46401,JAPAN

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1993年 / 115卷 / 24期

关键词：

D O I：

10.1021/ja00077a054

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

In the presence of 20 mol % of a chiral (acyloxy)borane (CAB) complex prepared from (2R,3R)-2-O-(2,6-diisopropoxybenzoyl)tartaric acid and borane-tetrahydrofuran, various allyltrimethylsilanes react with achiral aldehydes to afford the corresponding homoallylic alcohols in good yields with high diastereo- and enantioselectivities. Furthermore, the reactivity of allylation can be improved without reducing the enantioselelctivity by using 10-20 mol % of the CAB complex prepared from 3,5-bis(trifluoromethyl)phenylboronic acid and chiral tartaric acid derivative. The observed selectivities and re-face attack of nucleophiles on the carbonyl carbons of aldehydes imply that the extended transition-state model is applicable.

引用

页码：11490 / 11495

页数：6

共 30 条

[11]

FURUTA K, 1991, SYNLETT, P439

[12] ACYLOXYBORANE - AN ACTIVATING DEVICE FOR CARBOXYLIC-ACIDS [J].